| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $11,420.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $10,391.74 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $10,224.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $11,200.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $7,768.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $8,855.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $9,415.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $8,545.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $7,557.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $6,545.62 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $5,525.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $6,850.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $7,470.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $5,305.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $900.00 | PMC Rider |
| 2008 | $4,435.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $4,555.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $3,435.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $3,825.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $5,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $3,065.00 | Wellesley to Provincetown Inn (2-Day) |
| 2002 | $2,335.00 | Wellesley to Provincetown Inn (2-Day) |
| 2001 | $57,503.42 | Wellesley to Provincetown Inn (2-Day) |
| 2000 | $3,100.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1998 | $2,900.00 | Sturbridge to Provincetown Inn (2-Day) |
